Train Naked: Pierre du Plessis

Welcome to Episode 61 of The Incredible Machines podcast! In this thought-provoking conversation, Jon Oliff and Luke Holden sit down with Pierre du Plessis, a strategist, keynote speaker, coach (and co-consoirator), author and founder of Be Brave, a Cape Town based Strategy Design Lab.

Drawing on more than two decades of experience across strategy, design, human development and leadership, Pierre helps people and organisations find clarity, make brave decisions and navigate complexity. He is the author of four books, including Train Naked: A Guide to a Meaningful Life and Work That Matters, and the host of the Through the Fog podcast.

Pierre discusses the daily writing practice behind his newsletter, his journey from theology to professional speaking and the responsibility that comes with receiving another person’s attention. He also explores how leaders can use listening to help people feel seen, why myths and archetypes give us a framework for navigating life and what it means to show up without masks or pretence.

The conversation moves through philosophy, Japanese culture, mental health, depression, wolves and sled dogs, and Pierre’s current body of work, Only the Brave.   The episode is a powerful invitation to discover who you are, accept that you belong and decide what to do with your one wild and precious life.    ⏱ Timestamped Overview

00:33 – What Pierre would tell his younger self 07:32 – The story behind Pierre’s daily newsletter 13:21 – Theology, spirituality and writing multiple books 17:36 – Long form and short form media and how platforms shape thinking 27:12 – Algorithms, artificial intelligence and the loss of authentic expression 33:32 – Pierre’s journey into professional speaking 42:07 – Listening as a powerful and overlooked leadership skill 46:50 – The role of the jester in challenging authority and disrupting convention 50:40 – Doing difficult things and being willing to look foolish 55:12 – Japanese culture, and the philosophy of looking beyond the obstacle 1:00:24 – Archetypes, mythology and the search for identity 1:06:51 – Depression, introspection and the lifelong pursuit of self knowledge 1:13:26 – Pierre’s experience of antidepressants and emotional numbness 1:19:37 – Wolves, sled dogs and choosing between freedom and security 1:32:51 – Only the Brave and deciding what to do with your life 1:35:25 – What it really means to Train Naked 1:40:49 – Knowing that you belong and choosing how to use your one wild and precious life